Water → HCID 178481867, compound

HRID 1911058Notes

Reaction equation

HRID 1911058 reaction equation
Cl[C:2]1[C:3]2[S:23](=[O:24])[CH2:22][CH2:21][C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=1.[NH2:25][CH2:26][C:27]1[CH:28]=[C:29]([OH:33])[N:30]([CH3:32])[N:31]=1.C(N(C(C)C)CC)(C)C.O>O1CCOCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]3[N:7]=[C:2]([NH:25][CH2:26][C:27]4[CH:28]=[C:29]([OH:33])[N:30]([CH3:32])[N:31]=4)[C:3]4[S:23](=[O:24])[CH2:22][CH2:21][C:4]=4[N:5]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 594758954-Chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxideHCID 178481868HCID 178481868, compound

Product 1

HCID 178481867HCID 178481867, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

200 mg 4-chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide (cf Example 124), 313.3 mg 5-aminomethyl-2-methyl-2H-pyrazol-3-ol and 359.25 μl diisopropylethylamine are placed in 4 ml dioxane, heated to 130° C. in the microwave for 0.3 hours and for a further 0.3 hours to 130° C. Then the reaction mixture is mixed with water. The precipitated substance is suction filtered and washed with water. The product is purified by semipreparative HPLC (method A). 130 mg of the product are obtained as a powder. Analytical HPLC-MS (method B): RT=1.61 min.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customThe product is purified by semipreparative HPLC (method A)

Sources & evidence

ORD record
ord-891037eea299441dbe31a5079a0266c1
Source dataset
uspto-grants-2013_12
Patent number
US08604039B2

Reaction notes

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